Herbicide and method for controlling weeds

ABSTRACT

Herbicidal compositions containing (1) an alkyl Nphenylcarbamate, (2) 2-chloro-2&#39;&#39;, 6&#39;&#39;-diethyl-N(methoxymethyl)acetanilide, and (3) an aryl N-alkylcarbamate, an aryl N,N-dialkylcarbamate, or an aryl N-cycloalkylcarbamate are disclosed. An exemplary composition contains isopropyl N-(3chlorophenyl)carbamate, 2-chloro-2&#39;&#39;, 6&#39;&#39;-diethyl-N-(methoxymethyl)acetanilide, and 4-chlorophenyl N-methylcarbamate. These compositions are generally used for pre-emergent applications. The compounds may be applied together or separately.

United States Patent [191 Zick 1*Mar. 18, 1975 1 1 HERBICIDE AND METHOD FOR CONTROLLING WEEDS [75] Inventor: Warren H. Zick, Pittsburgh, Pa.

[73] Assignee: PPG Industries, Inc., Pittsburgh, Pa.

[ Notice: The portion of the term of this patent subsequent to Mar. 18, 1992, has been disclaimed.

[22] Filed: June 1, 1971 211 Appl. No.: 148,925

152] U.S.Cl ..7l/106,71/111,71/1l8- [51] Int. Cl A0ln 9/20 [58] Field ofSearch ..71/111,118

[56] References Cited UNITED STATES PATENTS 2,776,196 1/1957 Gysin et a1 71/111 X 2,776,197 1/1957 Gysin et al 71/111 X 2,812,247 11/1957 Gysin et al 71/111 X 3,547,620 12/1970 Olin 71/118 FOREIGN PATENTS OR APPLICATIONS phenylcarbamate, (2)

4/1970 United Kingdom ..71/111 9 OTHER PUBLICATIONS Canode et al., Weeds, Vol. 10, No. 3, pp. 216-219 Agnonomy Abstracts, 1965, P. 85.

Hunt, et all, Proceedings North Central Weed Control Conference, Dec. 9-11, 1969, Vol. 24, pp. 26-28 (cited by Applicant).

Primary E.\'aminer.1ames 0. Thomas, Jr. Attorney, Agent, or Firm-George D. Morris [57] ABSTRACT 20 Claims, N0 Drawings HERBlClDE AND METHOD FOR CONTROLLING WEEDS This invention relates to herbicidal compositions which contain at least one compound of each of the three following classes of compounds: (l) an alkyl N-phenyl-carbamate or mixtures of alkyl N- phenylcarbamates (Class I); (2) 2-chloro-2,6- diethyl-N-(methoxymethyl) acetanilide (Class 2) and (3) a compound which is an aryl N-alkylcarbamate, and aryl N,N-dialkylcarbamate, an aryl N-cycloalkylcarbamate, or mixtures thereof (Class 3).

The alkyl N-phenylcarbamates suitable for use in this invention may be represented by the structural formula:

R OCNH x wherein R is an unsubstituted alkyl or haloalkyl radical and X X X X and X are each independently hydrogen or halogen. The halogen substituents may be fluorine, chlorine, bromine, or iodine. Chlorine is preferred. The alkyl or haloalkyl radical usually contains from I to 8 carbon atoms although more may be used if desired. Most often the alkyl radical or haloalkyl radical contains from 1 to 3 carbon atoms. The isopropyl groups are preferred. Exemplary compounds are:

methyl N-phenylcarbamate ethyl N-phenylcarbamate propyl N-phenylcarbamate isopropyl N-phenylcarbamate butyl N-phenylcarbamate isobutyl N-phenylcarbamate sec-butyl N-phenylcarbamate tert-butyl N-phenylcarbamate phentyl N-phenylcarbamate 2,3-dimethylpropyl N-phenylcarbamate 3,3,4-trimethylpentyl N-phenylcarbamate octyl N-phenylcarbamate methyl N-(chlorophenyl)carbamate ethyl N-(2.5-dichlorophenyl) carbamate isopropyl N-(3-chlorophenyl) carbamate isopropyl N-(3-fluorophenyl carbamate isopropyl N-(3-bromophenyl) carbamate isopropyl N-(3-iodophenyl) carbamate butyl N-(2-chlorol4-bromophenyl) carbamate chloromethyl N-phenylcarbamate 3-bromobutyl N-phenylcarbamate 2,3-dichlorophenyl N-phenylcarbamate dichloromethyl N-(3-chlorophenyl) carbamate 1,2-dichloroethyl N-(4-bromophenyl) carbamate Of particular importance are the compounds isopropyl N-phenylcarbamate represented by the structural for- 3\CHOCNH and isopropyl N-(3-chlorophenyl)carbamate represented by the structural formula 3\ CHOCNH CH/ 1 l The alkyl N-phenylcarbamates -chlorobe prepared by the reaction of the appropriate alkyl haloformate and the appropriate aniline. Such reactions are well known as exemplified by US. Pat. Nos. 2.6l5.9l6 and 2,965,225.

The 2-chloro-2,6'-diethyl N-(methoxymethyl)- acetanilide may be represented by the structural formula CH2CH3 CHZCHB CH OCH R Aryl OCN/ 2 i ll wherein I Aryl is a'phenyl, substituted phenyl, naphthyl, or substituted naphthyl radical;

R is hydrogen, an unsubstituted alkyl radical, or a haloalkyl radical; and

R is an unsubstituted alkyl, haloalkyl, or cycloalkyl radical.

The halogen substituents may be fluorine, chlorine, bromine, or iodine. Chlorine is preferred. The aryl group is unsubstituted or may be substituted by halogen or by alkyl which usually contains from l to 8 carbon atoms. From 1 to 3 carbon atoms is more typical.

When Aryl is naphthyl, it may be either l-naphthyl or Z-naphthyl. The l-naphthyl radical is preferred. This applies whether the naphthyl radical is substituted or unsubstituted.

When R is unsubstituted alkyl or haloalkyl, it usually contains from l to 8 carbon atoms. From 1 to 4 carbon atoms are more typical. From 1 to 3 carbon atoms are preferred.

When R is unsubstituted alkyl or haloalkyl, it usually contains from 1 to 8 carbon atoms. From 1 to 4 carbon atoms are typical. From 1 to 3 carbon atoms are preferred.

When R is cycloalkyl, it usualfy contains from 3 to Exemplary compounds are: phenyl N-methylcarbamate phenyl N-ethylcarbamate phenyl N-propylcarbamate phenyl N-isopropylcarbamate phenyl N-butylcarbamate phenyl N-isobutylcarbamate phenyl N-sec-butylcarbamate phenyl N-tert-butylcarbamate phenyl N-hexylcarbamate phenyl N-octylcarbamate phenyl N-cyclohexylcarbamate 2-chlorophenyl N-methylcarbamate Z-chlorophenyl N-ethylcarbamate 2-chl0r0phenyl N-isopropylcarbamate 2-chlor0phenyl N-butylcarbamate 3-chlorophenyl N-methylcarbamate 3-chlorophenyl N-ethylcarbamate 3-chlorophenyl N-propylcarbamate 3-chl0r0phenyl N-isopropylcarbamate 3-chl0r0phenyl N-butylcarbamate 3-chlor0phenyl N-isobutylcarbamate 3-chl0r0phenyl N-sec-butylcarbamate 3-chlorophenyl N-tert-butylcarbamate 3-chlorophenyl N-pentylcarbamate 3-chlorophenyl N-octylcarbamate 4-chl0r0phenyl N-methylcarbamate 4-chlorophcnyl N-ethylcarbamate 4-chl0r0phenyl N-propylcarbamate 4-chlor0phenyl N-isopropylcarbamate 4-chlorophenyl N-butylcarbamate 4-chlorophenyl N-isobutylcarbamate 4-chl0r0phenyl N-sec-butylcarbamate 4-chl0rophenyl N-tert-butylcarbamate 4-chlorophenyl N-pentylcarbamate 4-chlorophenyl N-hexylcarbamate 4-chlorophenyl N-(3-methylpentyl)carbamate 4-chl0rophenyl N-heptylcarbamate 4-chlorophenyl N-octylcarbamate 4-chlorophenyl N-(2-ethylhexyl)carbamate 4-chlorophenyl N-cyclohexylcarbamate 4-chlorophenyl N-cyclohexyl N-methylcarbamate 4-bromophenyl N-methylcarbamate 4-bromophenyl N-ethylcarbamate 4-br0mophenyl-N-isopropylcarbamate 4-fluorophenyl-N-methylcarbamate 2,3-dichlorophenyl N-methylcarbamate 2,3-dichlorophenyl N-ethylcarbamate 2,3-dichlorophenyl N-propylcarbamate 2,3-dichlorophenyl N-hexylcarbamate 2,3-dichlorophenyl N-cycloheptylcarbamate 2,4-dichlorophenyl N-methylcarbamate 2,4-dichlorphenyl N-ethylcarbamate 2,4-dichlorophenyl N-butylcarbamate 2,4-dichlorophenyl N-sec-butylcarbamate 2,4-dichlorophenyl N-heptylcarbamate 2,4-dichloropheny] N-(2,3-dimethylpentyl)carbamate 2,4-dichl0r0phenyl N-cyclopropylcarbamate 2,5-dichlorophenyl N-methylcarbamate 2,5-dichlor0phenyl N-cthylcarbamate 2,6-dichlorophenyl N-methylcarbamate 2,6-dichlor0phenyl N-ethylcarbamate 2,6-dichlorophenyl N-isopropylcarbamate 2,6-dichlorophenyl N-sec-butylcarbamate 2,6-dichlorophenyl N-octylcarbamate 2,6-dichl0rophenyl N-cyclooctylcarbamate 2,6-dibrom0phenyl N-propylcarbamate 2,3,5-trichlorophenyl N-methylcarbamate 2,3,6-trichlorophenyl N-ethylcarbamate 2,3,4,6-tetrachlorophenyl N-methylcarbamate 2,3,4,5,6-pentachl0r0phenyl N-methylcarbamatc phenyl N,N-dimethylcarbamate phenyl N-methyl N-ethylcarbamatc phenyl N,N-diethylcarbamate phenyl N-isopropylcarbamate phenyl N-ethyl Nhexylcarbamate phenyl N-methyl N-octylcarbamate phenyl N,N-dioctylcarbamate 2-chlorophenyl N,N-dimethylcarbamate 2-chlorophenyl N-methyl N-ethylcarbamate 2-chlorophenyl N,N-diethylcarbamate 2-chlorophenyl N-methyl N-isopropylcarbamate 3-chlorophenyl N,N-dimethylcarbamate 3-chl0roph enyl N-methyl N-ethylcarbamate 3-chlorophenyl N,N-diethylcarbamate 3-chlorophenyl N-ethyl N-propylcarbamate 3-chlorophenyl N-methyl N-isopropylcarbamate 3-chlorophenyl N-butyl N-hexylcarbamatc 4-chl0r0phenyl N,N-dimethylcarbamate 4-chl0rophenyl N-methyl N-ethylcarbamate 4-chlor0phenyl N,N-diethylcarbamate 4-chlor0phenyl N-methyl N-propylcarbamate 4-chlor0phenyl N-methy] N-isopropylcarbamate 4-chlorophenyl N-methyl N-butylcarbamate 4-chlorophenyl N-ethyl N-isopropylcarbamate 4-chl0rophenyl N-ethyl N-butylcarbamate 4-chl0r0pheny] N-ethyl N-hexylcarbamate 4-chl0rophenyl N-ethyl N-(2-ethylhexyl)carbamate 4-chlorophenyl N-methyl N-(2-ethylhexyl)carbamate 4-chlor0phenyl N-methyl N-octylcarbamate 4-chlorophenyl N-hexyl N-octylcarbamate 4-chlorophenyl N,N-dioctylcarbamate 4-br0mophenyl N,N-dimethylcarbamate 4-bromophenyl N-methyl N-ethylcarbamate 4-bromopheny] N ,N-diethylcarbamate 2,3-dichiorophenyl N,N-dimethyl carbamate 2,3-dichl0r0phenyl N-methyl N-ethylcarbamate 2,3-dichlorophenyl N,N-diethylcarbamate 2,4-dichl0ro N,N-dimethylcarbamate 2,4-dichloro N-meth'yl N-ethylcarbamate 2,4-dichloro N,N-diethylcarbamate 2,4,5-trichlorophenyl N,N-dimethylcarbamate 2,4,5-trichl0r0phenyl N,N-diethylcarbamate 2,3,4,6-tetrachl0r0phenyl N,N-dimethylcarbamate 2,3,4,5,6-pentachlorophenyl N,N-dimethylcarbamate phenyl N-chloromethylcarbamate phenyl N-trichloromethylcarbamate phenyl N-(2-chlor0ethyl)carbamate phenyl N-(2;4-dichlorophentyl)carbamate 2-chlor0phenyl N-chloromethylcarbamate 2-chlorophenyl N-(3-chloropropyl)carbamate 3-chior0phenyl N-chloromethylcarbamate 3-chlorophenyl N-trichloromethylcarbamate 4-chlorophenyl N-chloromethylcarbamate 4-chlorophenyl N-dichloromethylcarbamate 4-chlorophenyl N-trichloromethylcarbamate 4-chlorophenyl N-(2-chl0roethyl)carbamate 4-chloropheny] N-(3,3-dichlor0pr0pyl)carbamate N-methyl 4-chlorophenyl N-(3-bromobutyl)carbamate 2,3-dichlorophenyl N-chloromethylcarbamate 2,4-dichlorophenyl N-dichloromethylcarbamate 2,3,4,5,6-pentachloro N-trichloromethylcarbamate phenyl N,N-bis(chloromethyl)carbamate phenyl N-methyl N-chloromethylcarbamate 2-chlorophenyl N-ethyl N-dichloromethylcarbamate 3-chlorophenyl N,N-bis(chloromethyl)carbamate 4-chlorophenyl N,N-bis(chloromethyl)carbamate 4-chlorophenyl N-methyl N-chloromethylcarbamate 4-chlorophenyl N-ethyl N-chloromethylcarbamate 4-chlorophenyl N,N-bis(2-chloroethyl)carbamate 4-chlorophenyl N-chloromethyl N-(2-chloroethyl)- carbamate 4-chlorophenyl N-( 1,2-dichloroethyl) perchloropropyl carbamate 2,4-dichlorophenyl N-methyl N-(2,2-dichloroethyl)- carbamate 2,3,5-trichlorophenyl carbamate l-naphthyl N-methylcarbamate l-naphthyl N-ethylcarbamate l-naphthyl N-propylcarbamate l-naphthyl N-isopropylcarbamate l-naphthyl N-butylcarbamate l-naphthyl N-isobutylcarbamate l-naphthyl N-sec-butylcarbamate l-naphthyl N-tert-butylcarbamate l-naphthyl N-pentylcarbamate l-naphthyl N-hexylcarbamate l-naphthyl N-octylcarbamate l-naphthyl N-cyclohexylcarbamate 3-chlorol -naphthyl N-methylcarbamate 3-chlorol -naphthyl N-ethylcarbamate 4-chlorol -naphthyl N-methylcarbamate 6-chlorol -naphthyl N-ethylcarbamate l-naphthyl N,N-dimethylcarbamate l-naphthyl N-methyl N-ethylcarbamate l-naphthyl N,N-diethylcarbamate 3-chloro-1-naphthyl N,N-dimethylcarbamate 7-chloro-1-naphthyl N,N-diethylcarbamate 4-chloro-1-naphthyl N-chloromethylcarbamate 4-chloro-l-naphthyl N,N-bis(chloromethyl)carbamate 2-naphthyl N-methylcarbamate 2-naphthyl N-ethylcarbamate Z-naphthyl N-isopropylcarbamate 2-naphthyl N-butylcarbamate 2-naphthyl N-octylcarbamate 3-chloro-2-naphthyl N-methylcarbamate 3,6,7-trichloro-2-naphthyl N-ethylcarbamate Z-naphthyl N,N-dimethylcarbamate 2-naphthyl N-methyl N-ethylcarbamate 2-naphthyl N,N-diethylcarbamate 3,6chloro-2naphthyl N,N-dimethylcarbamate Pat.

4-chloro-2-naphthyl N-methyl N-chloromethylcarbamate 6-chloro-2-naphthyl N,N-bis(2-chloroethyl)carbamate Of particular importance are the compounds:

phenyl N-methylcarbamate,

N,N-bis( trichloromethyl 4-chlorophcnyl N-methylcarbamate,

C l OCNHCH 4-chlorophenyl N-ethylcarbamate,

C 1 OENHCH CH 4-chlorophenyl N,N-dimethylcarbamatc,

ca 01 o t m 3 0 3 4-chlorophenyl N-butylcarbamate,

Cl OCNHCH CH CH Cl-l 4-chlorophenyl N-cyclohexylcarbamate,

C 1-@ OfiNl-l E l-naphthyl N-methylcarbamate,

Of these, 4-chlorophenyl N-methylcarbamate is preferred.

The aryl N-alkylcarbamates and the aryl N,N-dialkylcarbamates may be prepared by reacting the appropriate chloroformate with a primary or secondary amine. Such reactions are well known as exemplified by U.S. Pat. Nos. 2,776,197; 2,812,247; 2,903,478; and British Patent Specification No. 1,042,203.

The aryl N-alkylcarbamates and the aryl N,N-dialkylcarbamates may be prepared by reacting the appropriate chloroformate with a primary or secondary amine. Such reactions are well known as exemplified by U.S. Pats. No. 2,776,197; 2,812,247; 2,903,478; and British Patent Specification No. l,O42,203.

The aryl N-alkylcarbamates and the aryl N,N-dialkylcarbamates may also be prepared by reacting the appropriate phenol or naphthol with the appropriate alkyl carbamyl chloride or dialkyl carbamyl chloride. These reactions are illustrated by U.S. Pat. No. 2,812,247 and British Patent Specification No. 1,042,203.

A third method for preparing the aryl N- alkylcarbamates is the reaction of the appropriate phenol or naphthol with an alkyl isocyanate. This class of reaction is exemplified by U.S. Pat. No. 3,426,064 and British Patent Specification No. 1,042,203.

It has been found that compositions containing one or more compounds of each of the three classes described above possess herbicidal activity. These compositions are usually applied to the soil as preemergence herbicides but may be applied to the soil or plant for post-emergence herbicidal purposes.

A single composition containing members of the three classes may be applied to the soil or plant. Alternatively, the members may be applied separately within a reasonable interval of time which will allow cooperation between the members to produce the desired effect. Of course, the members may be combined in various ways for application, as, for example, separate applications of a member of one class and a combination of members of the remaining two classes may be made.

In one embodiment of this invention the herbicidal composition may be used for control of weeds by preemergent applications. In one form of pre-emergent application, the composition is applied to the soil and/or weeds subsequent to seeding the crop plants but prior to the emergence of the crop seedling through the soil. While the amounts applied are ordinarily as hereinafter described, it may generally be stated that greater amounts of the composition may be used as the crop seed is positioned deeper in the soil.

In another embodiment, the formulation is applied to the soil close to, but not directly above the seed. This may be achieved for now crops by applying the formulation as one or more sidebands.

In still another embodiment, the formulation is applied as a layer below the surface of the soil. The layer may conveniently be located above or below the seed, depending upon the tolerance of the seed. Subsoil layering can also be used for the control of perennial weeds growing with established herbaceous or woody crops.

In another form of pre-emergent application, the composition is applied to the soil and/or weeds concurrently with the application of the crop seed. Here the seed and composition may be applied by separate systems or the seed and the composition may be mixed and applied by the same system. When the composition and seeds are mixed prior to application, it is usually desirable than the herbicidal composition derivative be in the form of a flowable solid such as crystals, powder, or granules.

In a further form of pre-emergent application, the herbicidal composition is incorporated in the soil or applied to the soil and/or weeds prior to the planting of crops. This method permits additional flexibility because amounts of composition in excess of the amount which would kill or retard the crop plant may be applied if desired. Sufficient time is then allowed for the composition concentration to abate to safe levels. Crop plants or seeds may then be set out. The pre-plant, soil incorporate method is often used to achieve control of deep-germinating weeds.

It is often advantageous to apply the herbicidal composition post-emergence to the area containing weeds and crop plants which have emerged from the soil. In this fashion, some weeds are selectively killed without significant damage to crop plants. The selectivity effect is enhanced if the crop plants are well established whereas the weeds are not.

In a further form of post-emergence application, the herbicidal composition is applied to the area containing weeds and crop plants which have emerged from the soil. The application rate is adjusted so that the growth of the weeds is inhibited while the crop plant suffers no significant damage. The rate of application is generally less than when a killing of the weeds is desired.

The amounts of the three classes which are applied in the above embodiments may vary widely. The amount of Class 1 applied usually is in the range of from 0.1 to 50 pounds per acre. Usually the amount is in the range of from 0.5 to 20 pounds per acre. A range of from 1 to 10 pounds per acre is preferred. The amount of Class 2 applied is usually in the range of from 0.1 to 50 pounds per acre. Ordinarily the amount is in the range of from 0.5 to 20 pounds per acre. A range of from 1 to 10 pounds per acre is preferred. The amount of Class 3 applied usually ranges from I to 100 percent of the rage at which Class 1 is applied. Typically the application is in the range of 4 to 50 percent. A range of from 5 to 30 percent is preferred. While these general ranges of application are applicable to the above embodiments, it is recognized that both the optimum and useful amounts will vary depending upon the plant crop involved, the weeds encountered, the particular compounds used, the soil condition, cultivation practices, and the effect desired. The Examples give an even better indication of the amounts of the classes which may advantageously be used when dealing with certain weeds.

The proportions of the classes in a composition con-' taining the three classes may also vary widely. Generally speaking, the herbicidal composition contains herbicidally effective amounts of both the alkyl N-phenyl carbamate or mixtures thereof and the 2-chloro-2',6'- diethyl N-(methoxymethyl)acetanilide and, further, an aryl N-alkylcarbamate, an aryl N,N-dialkylcarbamate, an aryl N-cycloalkylcarbamate, or mixtures thereof in an amount sufficient to extend the soil life of the alkyl N-phenyl carbamate. Typically, the Class 1 Class 2 weight ratio is in the range of from 1:500 to 500:1. A range of from 1:40 to 40:1 is more usual. The preferred range is from 1:10 to 10:1. Equal amounts are commonly employed. The Class 1:Class 3 weight ratio is ordinarily in the range of from 1:1 to 100:1. A range of from 2:1 to 25:1 is typical. The preferred range is from 3:1 to 20:1.

The herbicidal composition may be formulated in many ways. Convenient formulations include granular formulations, wettable powders, solutions, and emulsions. These formulations may be prepared in accordance with the general techniques well known to the art. These formulations may be applied directly to the soil and/or weeds or they may be diluted-before application.

Generally speaking, formulations contain from about 0.1 to 100 percent by weight members of the three classes constituting collectively what may be termed actives. Often formulations contain from about 1 to about 50 percent by weight actives. Of course, the precise amount will depend upon such factors as the type of formulation employed, the type of application, and the mode of application.

Suitable wettable powders typically contain from about 1 to about 100 percent by weight actives. Ordinarily, wettable powders contain from 10 to per cent by weight actives. The actives may be admixed with an inert powder such as silica, chalk, talc, limestone, or clay. Any convenient amount of diluent may be used, from about 15 to about per cent being typical. Small amounts of dispersing and/or wetting agents are usually included in the formulations. These usually range from 0.1 to 15 per cent by weight of the formulation. Ordinarily amounts ranging from 1 to 12 per cent are used.

The wettable powder is typically dispersed in water for application.

Solutions of the actives may be prepared. Ordinarily concentrated solutions are prepared which, when diluted with water for application, form emulsions. Solvents suitable for use are numerous and include many well known for their solvency powers. Examples in clude the xylenes, toluene, methyl alcohol, ethyl alcohol, isopropyl alcohol, the butyl alcohols, water, gasoline, kerosene diethyl ether, methyl ethyl ether, ethylene glycol, propylene glycol, n-amyl acetate, allyl alcohol, cellusolve, methyl acetate, ethyl acetate, acetone, methyl ethyl ketone, methyl isobutyl ketone, benzene, methyl naphthalene, ethyl naphthalene, and edible oils such as corn oil, olive oil, cod liver oil, cottonseed oil, safflower oil, soybean oil, and peanut oil.

The formulations of the present invention frequently include small amounts of various surfactants such as wetting agents, emulsifiers, and dispersants. Anionic surfactants are used for wettable powders. Emulsifiable concentrates generally contain blends of ionic and anionic surfactants. Many surfactants are available as commercial products. Well known dispersing agents which are useful in wettable powders include the lignin surfactants (ligno sulfonates) such as those described in U.S. Pat. No. 2,491,832, and the alkyaryl sulfonates. The ligno sulfonates of most interest are the metallic, notably the sodium and calcium, sulfonate salts. Molecular weights of these materials normally range from about 1,000 to about 20,000. Another useful class of surfactants comprises the formaldehyde-naphthalene sulfonate condensates typified by those disclosed in US. Pat. No. 2,516,095. Other useful dispersing agents are found among the alkali metal derivatives of unsaturated and aromatic hydrocarbons, the akali metal alcoholates of long chain alcohols, and the anhydrous alkali metal soaps of higher fatty acids. Particularly suitable wetting agents for wettable powders are the taurates typified by sodium N-methyl-N-oleoyl taurate. Sodium alkyl naphthalene sulfonates and the oleic acid ester of sodium isothionate are also especially useful. The condensation products of alkylene oxides with phenols and organic acids, the polyalkylene derivatives of sorbitan esters, complex ether alcohols, and mahogany soaps are examples of useful ionic surfactants. Other surface active agents of the same or similar physical properties are known to the art and can be employed in the formulations of this invention.

It is often desirable to include in a formulation which is to be mixed with water, a small amount, e.g., about 1/10 to about 1 per cent by weight of a suitable antifoaming agent. Useful anti-foaming agents include the ditertiary acetylenic glycols, such as those marketed under the tradename SURFYNOL by Air Reduction Chemical and Carbide Company, 150 E. 42nd Street, New York, NY. 10017. Other compounds known to the art to function as anti-foaming agents may be employed if desired. Such compounds include 2-octonol, sulfonated oils, and silicones. Useful silicones are those of low molecular weight, i.e., the silicone fluids or oils. Typical of these are the methyl and ethyl substituted siloxanes such as the dimethyl siloxanes.

Many of the solvents, solvent systems, and wetting agents are discussed in US. Pat. Nos. 2,695,225 and 3,330,642 and Canadian Pat. No. 851,658.

The amount of actives in liquid formulations, include both single phase solutions and emulsions containing the three classes, is subject to wide variation. The liquid may contain the actives in very dilute concentrations, although it is ordinarily not so dilute that excessive amounts of solvent must be applied in order to achieve application of a useful amount of the actives. The lowest practical concentration for most purposes is the concentration at which the formulation is applied to the soil and/or weeds. The upper limit of concentration is the solubility limit of the actives in the solvent or solvent system used. This will, of course, depend upon the identities of the members of the three classes, the identity of the solvent system, and the highest temperature for which precipitation of solids is acceptable. It is ordinarily desirable to form a concentrated liquid formulation, usually an emulsifiable concentrate or concentrated emulsion, of the actives which will not show precipitation above about 20F., and, more preferably, above about 10F. A broad range of concentration for the actives in a liquid formulation is from 0.05 percent to 90 percent by weight. Liquid concentrates generally contain from about 10 percent to about percent by weight actives. From about 35 percent to about 55 percent is preferred. Liquid formulations generally contain from about 0.05 percent to about 70 percent actives at the time of application. Typically, the range is from 0.1 to 10. From about 0.5 percent to 5 percent is preferred. It has been found that isopropyl N(3-chlorophenyl)- carbamate aids in dissolving 2-chloro-2',6-diethyl-N- (methoxymethyl)acetanilide. As a result, xylene solutions of isopropyl N-(3-chlorophenyl)carbamate, 2- chloro-2',6-diethyl'-N-(methoxymethyl)acetanilide and 4-chlorophenyl N-methyl carbamate having unusually high concentrations of these three compounds may be prepared. An example of a liquid concentrate is as follows:

Granular formulations may be prepared by spraying molten mixtures of the three classes directly onto an inert carrier. The classes may be applied sequentially if desired as a melt. In another method, a liquid formulation, either a solution or an emulsion, may be applied to the inert carrier particles. For instance, the formulation exemplified in the previous paragraph is suitable for application to inert carrier particles. Formulations of the three classes may also be applied sequentially. As an example, a solution of 2-chloro-2,6',-diethyl N-(methoxymethyl)acetanilide dissolved in xylene may be applied to inert carrier particles, after which the impregnated particles are dried. Isopropyl N-(3-chlorophenyl)carbamate and 4-chlorophenyl N- methylcarbamate dissolved in an organic solvent such as xylene are then applied to the particles. If desired, the isopropyl N-(3-chlorophenyl)carbamate and the 4-chlorophenyl N-methylcarbamate may be applied as separate solutions. Many types of inert carrier particles are suitable for use in the instant invention. Among these are attapulgite, montmorillonite, bentonite, vermiculite, corn cobs, and sawdust. The actives ordinarily constitute from about 0.5 to about 50 percent by weight of these granular products. Typically, the actives content ranges from about 1 to about 35 percent by weight. From about 10 to about 30 percent is preferred. An example of a granular formulation which may be used is the following:

lsopropyl N-(3-chlorophenyl)carbamate 10% w/w 2-Chloro 2,6'-diethyl N-(methoxymethyl) acetanilide l 4'Chlorophenyl N-methylearbamate 2.5 Xylene w/w Montmorillonite 72.5

The compositions of the invention are especially suitable for the elimination of weeds in onion patches and soybean fields. Seeded onion patches are ordinarily treated pre-emergence the onion plants and once or twice after the onions have emerged. Seeded soybean fields are ordinarily treated pre-emergence to the soybean plants.

EXAMPLE 1 Sandy loam soil having (1) a mechanical analysis of 62 percent sand, 30 percent silt and 8 percent clay, (2) an inherent organic matter level of 3.6 percent, and (3) of pH of 6.1 was modified by adding 2.0 percent by weight peat, 5.3 percent by weight dried cow manure, and sufficient lime to increase the pH to approximately 7.0. The modified soil was sprayed with solutions of the test compounds. For each pound per acre reported in the results, 5.5 micrograms of test compound were applied to 1 gram of soil. The test compounds were then incorporated into the soil by mechanical blenders. The treated soil and untreated control soil were stored under moist conditions at room temperature. Aliquots of soil were removed from each soil 1, 2, 4 and 8 weeks after treatment and placed in a 3 inch by 3 inch pot over a layer of untreated, sterilized soil. The depth of the treated soil in the pot was 3/4 inch. Each pot was then seeded with test plants. After a growing period of approximately 4 weeks, the herbicidal effectiveness of the test composition was evaluated and the results reported on a scale ranging from 0 (no injury) to"l0 (all plants killed). The results are shown in Table l where the test compositions are rates of application are identified according to the following key:

4-Chlorophenyl N-methylcarbamate The test plants used are identified according to the following key:

identification Code Test Plant QKGS Quaekgrass (Agropyron repens [L.] Beauv.) WOAT Wild Oats (Avena fatua L.)

BNGS Barnyardgrass (Eclzirwchlou crurgulli [L.]

Beauv.)

CBGS Crabgrass (Digilaria sanguinulis Soop.) BKWT Buckwheat (Pulygzmum r'vnvolvulur L.) MNGY Morning Glory (Mixture of Ipomuea purpureu Roth and lpumoea Iiederaceu .lacq.)

TABLE 1 BIOASSAY OF HERBlClDAL COMPOSITIONS USING SEVERAL TEST PLANTS Test Injury Rating Composition lntcrval and Rate Weeks QKGS WOAT BNGS CBGS BKWT MNGY A l 0 0 0 O 0 0 B 1 l0 l0 8 2 l() 8 C l 9 8 7 l0 0 0 D l 10 8 7 l0 0 0 A 2 0 0 O O O U C 2 9 8 l0 l0 0 O D 2 l0 8 9 l0 0 0 E 2 l0 l0 8 5 l0 8 F 2 l0 l0 l0 10 ll) 7 l) 4 5 5 6 9 t) (l E 4 ll) l0 7 3 J 8 l W m u in u s t S 5 5 7 6 (I (I l) 8 5 5 6 5 (t (I F 8 10 ll) 8 6 l0 8 EXAMPLE ll The procedure of Example I is used to determine the herbicidal effectiveness of compositions containing isopropyl Nphenylearbamate instead of isopropyl N-(.l-ehlorophenyl)carbaniate. The results are shown in Table 2 where additional test compositions and rates of application are identified according to the following key:

The data for compositions A, C, and D of Example I are included in Table 2 for ease in comparison. Test plants are the same as those of Example I.

EXAMPLE in Field plots were prepared in Colo silt loam soil having an organic matter content ot approximately 3.5 percent. the plots were then seeded with soybeans ((ily cine max [L.] Merr.). Before the soybeam plants emerged, several plots were treated with various test compounds. Thirty-seven days after treatment the plots were evaluated for weed control. The results are reported as percent control as compared to untreated control plots and are the mean of four replicates. Major weed species present were redroot pigweed (Amaranthus retroflexus L.), yellow foxtail (Setaria glauca [L.] Beauv.), giant foxtail (Setaria faberii Herrm.), Pennsylvania smartweed (Polygonum pennsylvanicum L.) and velvetleaf (Abutilon theophrasti Medic). Yields are also reported. Untreated, hand-weeded plots are maintained as a check on yields. The identity of the test compounds, their rates of application and the xssy ia sshsmn in T99 a Table 3 Field Trials of Various Herbicidal Compositions Applied Pre-Emergence to Soybeans Rate Percent Percent Major Species Yield Control Control Test Compound lb/A of Broadleaf of Foxtail Not Controlled Bushels/A 2-Chloro-2'.6-Diethyl N-(Meth0xymethyl)- 2 50 90 Velvetleaf, Pa. 5] Acetanilide Smartwced lsopropyl N-(3-Chlorophenyl)carbamatc 2.5 5 5 4l 4-Chlorophenyl N-methylcarbamate 0.625 2-Chloro-2,6'-Diethyl N-(Methoxymethy|)- l 85 86 Velvetlcal' 56 Acetanilidc lsopropyl N (3Chlorophenyl)carbamate 2.5 4-Chlorophenyl N-Mcthylcarhamate 0.625 lsopropyl N-(3-Chlorophenyl )earbamate 5.0 5 38 42 4-Chlorophcnyl N-Methylcarbamate 1.25 2-Chloro2,6-Diethyl N-( Methoxymcthyl)- l 81 82 Velvctleaf 55 Aeetanilide lsopropyl N-(3-Chlorophenyl )carbamate 5.0 4-Chlorophenyl N-Methylcarbamate l.25 Hand-weeded Check I00 I00 54 TABLE 2 BIOASSAY OF HERBICIDAL COMPOSlTlONS USING SEVERAL TEST PLANTS Test Injury Rating Composition Interval,

and Rate Weeks QKGS WOAT BNGS CBGS BKWT MNGY A l 0 O 0 0 0 O. G 1 l0 l0 0 0 l0 4 C l 9 8 7 l0 0 0 D 1 l0 8 7 l0 0 0 H 1 l0 l0 0 0 l0 7 l l l0 l0 l0 l0 l0 10 A 2 0 O 0 0 0 0 G 2 l0 l0 0 0 9 2 C 2 9 8 l0 l0 0 0 D 2 l0 8 9 l0 0 0 H 2 l0 l0 0 0 l0 7 l 2 l0 l0 l0 l0 9 7 A 4 0 0 0 O 0 0 G 4 9 8 3 O 9 0 C 4 5 5 6 9 2 2 D 4 5 5 6 9 0 0 H 4 l0 l0 3 0 9 5 l 4 l0 l0 7 l0 9 8 A X (l (l (l (l (J t) (i 8 l) 0 (l (l (l 0 X 5 5 7 6 (l 0 D 8 5 5 6 5 t) (J H 8 10 It) 0 O 9 5 l 8 l0 l0 8 7 9 8 EXAMPLE IV A single-herbicide study and a herbicide combination study were conducted in separate but adjacent field studies on the same plot area which is composed of Weir silt loam having 1.0 percent organic matter. A randomized complete block design with three replications was used for each study. Individual plots were 35 feet long, 4 rows wide, with a 30-inch row spacing. Three of the four rows were treated, the fourth serving as a weedy check. A four-row weedy and a four-row weed-free plot were included in each of the studies. Preplant incorporate (PPl) treatments of both single herbicides and herbicide combinations were applied in the late spring and immediately incorporated with a tandem disc to a depth of 3 to 4 inches followed by a spike-tooth harrow. Soybeans (Glycine max L. var. Clark 63) were planted in both the preplant incorporate test area and in the area where the single-herbicide preemergence (PE) treatments were to be applied. The preemergence treatments using single herbicides were applied on the same day, hereinafter referred to as the base day. One day after the base day, several other plots were planted in the same variety of soybeans and immediately thereafter the pre-emergence treatments of herbicide combinations were applied. All treatments were applied in 20 gallon of water per acre. All plots were visually rated for weeds days after the base day. The four-row weedy check and the weedy single rows associated with each plot were used in evaluating the three treated rows. Observations continued throughout the season and a weed count in the fourrow weedy check plot was made 92 days after the base day. This weed count is presented in Table 4. Ten feet of the middle treated row was harvested 134 days after the base day. All yields are converted to a uniform 18.0 percent moisture basis. the identity of the test compounds, their rates and modes of application, weed control, crop injury and yields are shown in Tables 5 and 6 for single herbicides and herbicide combinations, respectively.

Table 4 Weed Species Populations in the Four-Row WeedyCheck Plots in Weeds Per Square Yard Table 5 Weed Control, Crop lnjury and Soybean Yield as Influenced by Single Herbicide Compositions Test Composition and Rate, Crop Yield Weed Control at Weed Escapes Mode of Application lb/A lnjury Bu/A 40 Da 5 Grass road- Leaf 2-Chloro-2',6'-Diethyl-N-(methoxymethyl)aeetanilide, PE 2.5 3 45.6 99 90 L0, MG lsopropyl N-(3-Chlorophenyl)earbamate, PE 40 10 29.0 97 77 L0, PW, RW lsopropyl N-( 3-Chlorophenyl)earbamate, PE 2.0 0 29.5 93 L0, PW, RW 4-(hlorophenvl N-meth lcarhamate, PE 05 lsopropyl N-(3-(hlorophenyl)earhamate, PE 4.0 6 33.9 97 83 [-Q, RW 4('hloropl|enyl N-Methylcarbamate, PE 1.0 Z-(hloro-Z,6'-Diethyl-N-(Methoxymethyl)aeetanilide, PH 2.5 0 35 5 98 L0. RW lsopropyl N-(3-Chlorophenyl)carhamute. PPI 4.0 3 21.7 70 53 L0, PW, RW lsopropyl N-(3-(hlorophenyl)curbamate, PH 2.0 0 20.9 70 43 L0, PW, RW 4-(hloro henyl N-meth learhumate, PH 0.5 lsopropy N'( -Chlorop enyl)carhamute, PH 4.0 10 16.8 95 RW 4-(hlorophenyl N-Methylearbumate, PPl l.0 WLCLLFI'CC Cheek 0 51.9 I00 I00 Weedy Check 0 21.8 0 LQ predominant '(rup injury values refer to percent stunting.

"Weed Species Present:

l-'I (ireen and Yellow Foxtail (St'luriu \irizlix [L.] Beauv. and Seluriu glam'u |l lleauv.)

Dominant species was Lamhs'quarter with (ommon Ragweed and Retlroot Pigweetl next. Nutsetlge population was not uniform, thereby precluding a fair rating nt'this weed.

Table 6 Test Composition and Rate, Crop Yield Weed Control at Weed Escapes Mode of Application lb/A Injury Bu/A 40 Days Grass Broad- Leaf 2-Chloro-2,6-Diethyl-N-(Methoxymcthyl)acetanilide, PE 1.5 3 49.4 96 91 L0, RW lsopropyl N-(3-Chlorophenyl)carbamate, PE 1.5 Z-Chloro-Z,6'-Diethyl-N-(Methoxymethyl)aeetanilide, PE 2.0 50.0 98 96 RW lso ropyl N-(3-Chlorophenyl)carbamate, PE 2,0 2- blurb-2,6'-Diethyl-N-(Methoxymethyl)acetamlide, PE 2.0 lso ropyl N-(3-Chlorophenyl)carbamate, PE 1.5 0 54.3 99 94 LO 4 hlorophenyl N-methylcarbamate. PE 0.375 2-Chloro-2.6 -Dietltyl-N-(Methoxymethyl)acetamlide. PPl 2.0 lsopropyl N-(B-Chlorophenyl)carbamate. PH 1.5 0 25.5 89 60 L0, PW -l-Clilorophenyl Nmetl'lylcarbamate. PPl 0.375 Weetl-lrec Check 0 50.5 l()() l()() Weedy Check O 20.9 0 0 All SPP.

Crop injury values refer to percent stunting vs. \veetHrce check.

Weed species present same as FNZ, Table 5. Dominant species was Lamhsquarter which constituted almost a solid stand in the l'our-row weedy check plots. Other listetl species become more common where herbicides controlled Lambsquarter partially or completely. Nutsedgc population was not uniform. thereby precluding a valid rating.

EXAMPLE v A field study of the effect of the pre-emergence application of single herbicides and herbicide combinations was conducted in Decorra silt loam having an organic matter content of 2.5 percent. Individual plots were 398 feet long and 12 rows wide with a row spacing of inches. One of the plots was an untreated check. in the late spring, the plots were planted in soybeans Table 7 Weed Control and Crop Injury As Influenced by Test Compositions Thirty-Five Days After Application Test Composition Weed Control Broad- Weed Escapes Leaf Rate, Lb/A Crop Injury Grass 2-Chloro-2',6'-Diethyl-N-(Methoxymethyl)anilide lsopropyl N-( 3-Chlorophenyl )carbamate lsopropyl N-(3-Chlorophenyl)carbamate 4-Chlorophcnyl N-Methylearbamate 2-Chloro-2'.6 -Diethyl-N-(Methoxymethyhanilidc lsopropyl N-(3-Chlorophenyl)carbamate Z-Chloro-Z.6'-Diethyl-N-(Methoxymethyhanilide lso ropyl N-( 3-Chlorophenyl )carbamate 4- hlorophenyl N-Mcthylcarbamate Untreated Control SW. JW. LO, RW, 'VL, GF MW, YN MW, CH. .lW, GF, YN

0 99 CH. GF

SW, .lW. GF (95% OF) Table 8 Weed Control Any Yield as Influenced by Test Compositions at Harvest One Hundred Twenty-Five Days After Application Weed Control Rate, Yield, Broad- Weed Escapes Test Composition Lb/A Bushels/A Grass Leaf 2-Chl0ro-2,6-Dicthyl-N-(Mcthoxymethyhanilide 2 99 JW, SW lsopropyl N-(3-Chlorophcnyl)carbamate 4 42 85 FT, MG, SF lsopropyl N-(3-Chlorophenyl)carbamate 4 4L8 85 85 MG, GF. YN

Table 8 -Continued Weed Control Rate, Yield, Broad- Weed Escapes Tcst Composition Lb/A Bushels/A Grass Leaf 4-Chlorophenyl N-methylcarbamate l 2-Chloro-2',6'-Dicthyl-N-(Methoxymcthyl)anilidc 1.5 40.5 98 90 JW (Stunted) lsopropyl N-(3'Chlorophenyl)carbamatc 2 2-Chloro2',6-Diethyl-N-( Mcthoxymethyl )anilidc 1.5 lfiplOpyl N-(3-Chlorophenyl)carbamatc 2 43 98 98 .IW (Stunted) 4- hlorophenyl N-Methylcarbamate 0.5

0 0 GF, SW, etci Untreated Control Abbreviations same as Table 7i "Impossible to harvest because of weeds.

I claim:

1. A herbicidal composition containing herbicidallyeffective amounts of both an alkyl N-phenylcarbamate or mixtures of alkyl N-phenylcarbamates and 2-chloro- 2,6-diethyl N-methoxymethyl)acetanilide and further containing a commpound selected from the group consisting of aryl N-alkylcarbamate, aryl N,N-dialkylcarbamate, aryl N-cycloalkylcarbamate, and mixtures thereof in an amount sufficient to extend the soil life of said alkyl N-phenylcarbamate or mixtures of alkyl N- phenylcarbamates.

2. A herbicidal composition containing herbicidallyeffective amounts of both a. an alkyl N-phenylcarbamate or mixtures of alkyl N-phenylcarbamates represented by the structural formula R OENH X wherein Aryl is phenyl, substituted phenyl, naphthyl, or

substituted naphthyl;

R is hydrogen, unsubstituted alkyl or haloalkyl;

and

R is unsubstituted alkyl, haloalkyl, or cycloalkyl;

in an amount sufficient to extend the soil life of said alkyl N-phenylcarbamate or mixtures of alkyl N- phenylcarbamates.

3. The herbicidal composition of claim 2 wherein a. R, contains from 1 to 8 carbon atoms;

b. R; is hydrogen, unsubstituted alkyl containing from I to 8 carbon atoms or haloalkyl containing from I to 8 carbon atoms; and

c. R is unsubstituted alkyl containing from I to 8 carbon atoms, haloalkyl containing from l to 8 carbon atoms or cycloalkyl containing from 3 to 8 carbon atoms.

4. The herbicidal composition of claim 3 which contains from about 0.1 to about percent by weight actives.

5. The herbicidal composition of claim 4 wherein a. the weight ratio of said alkyl N-phenylcarbamate or mixtures of said alkyl N-phenylcarbamates to said 2-chloro-2,6-diethyl N-(methoxymethyl- )acetanilide present in the composition is in the range of from 1:500 to 500:1; and

b. the weight ratio of said alkyl N-phenylcarbamate of mixtures of said alkyl N-phenylcarbamates to said compound or mixtures of said compounds present in the composition is in the range of from 1:1 to 100:1.

6. The herbicidal composition of claim 5 wherein said alkyl N-phenylcarbamate is isopropyl N- phenylcarbamate.

7. The herbicidal composition of claim 6 wherein said compound is selected from the group consisting of halophenyl N-alkylcarbamate, halophenyl N,N-diallylcarbamate, and hzflophenyl N-cycloalkylcarbamate.

8. The herbicidal composition of claim 6 wherein said compound is selected from the group consisting of 4-chlorophenyl N-alkylcarbamate, 4-chlorophenyl N,N-dialkylcarbamate, and 4-chlorophenyl N-cycloalkylcarbamate.

9. The herbicidal composition of claim 6 wherein said compound is selected from the group consisting of phenyl N-methylcarbamate, 4-chlorophenyl N- methylcarbamate, 4-ehlorophenyl N-ethylcarbamate,

4-chlorophenyl N,N-dimethylcarbamate, 4- chlorophcnyl- N butylcarbamate, 4-chlorophenyl N-cyclohexylcarbamate and l-naphthyl N- 4-chlorophenyl N ,N-dimcthylcarbamate, 4- chlorophenyl N-butylcarbamate, 4-chlorophenyl N-cyclohexylcarbamatc and l-naphthyl N- methylcarbamate.

14. A method of controlling weeds comprising applying to soil containing weeds a. a herbicidal amount of an alkyl N- phenylcarbamate or mixtures of alkyl N- phenylcarbamates;

b. a herbicidal amount of 2-chloro-2',6-diethyl N-(methoxymethyl)acetanilide; and

c. a compound or mixture of compounds selected from the group consisting of aryl N- alkylcarbamate, aryl N,N-dialkylcarbamate, and aryl N-cyclohexylcarbamate in an amount sufficient to extend the soil life or said alkyl N- phenylcarbamate or mixtures of alkyl N- phenylcarbamates.

15. The method of claim 14 wherein said alkyl- N- phenylcarbamate or mixtures of alkyl N-phenyl carbamates is applied at a rate in the range of from 0.1 to 50 pounds per acre, said 2-chloro-2',6-diethyl N-(methoxymethyl)acetanilide is applied at a rate in the range of from 0.] to 50 pounds per acre and the compound or mixture of compounds is applied at a rate which is from 1 to 100 percent of the rate at which the alkyl N-phenylcarbamate is applied.

16. The method of claim 15 wherein the application is a pre-emergence application.

17. The method of claim 15 wherein said alkyl N- phenylcarbamate or mixtures of alkyl N phenylcarbamates are selected from the group consisting of isopropyl N-phenylcarbamate and isopropyl N-(3-chlorophenyl)carbamate and said compound or mixtures of compounds are selected from the group consisting of phenyl N-methylcarbamate, 4- chlorophenyl N-methylcarbamate, 4-chlorophenyl N- ethylcarbamate, 4-chlorophenyl N-butylcarbamate, 4- chlorophenyl N,N-dimethylcarbamate, 4-chlorophenyl N-cyclohexylcarbamate, and l-naphthyl N- methylcarbamate.

18. A herbicidal composition containing herbicidally-effective amounts of both isopropyl N- phenylcarbamate and 2-chloro-2,6-diethyl N-(methoxymethyl)acetanilide and further containing 4-chlorophenyl N-methylcarbamate in an amount sufficient to extend the soil life of said isopropyl N- phenylcarbamate.

19. A herbicidal composition containing herbicidally-effective amounts of both isopropyl N-(3-chlorophenyl)carbamate and 2-chloro-2,6- diethyl N-(methoxymethyl)acetanilide and further containing 4-chlorophenyl N-methylcarbamate in an'amount sufficient to extend the soil life of said isopropyl N-(3- chlorophenyl) carbamate.

20. A herbicidal liquid concentrate comprising'about 33.5 percent by weight isopropyl N-(3-chlorophenyl) carbamate, about 33.5 percent by weight 2-chloro- 2',6'-diethyl N-(methoxymethyl)acetanilide, about 8.3 percent by weight 4-chlorophenyl N-methylcarbamate and about 14.1 percent by weight xylene. 

1. A HERBICIDAL COMPOSITION CONTAINING HERBICIDALLYEFFECTIVE AMOUNTS OF BOTH AN ALKYL N-PHENYLCARBAMATE OR MIXTURES OF ALKYL N-PHENYLCARBAMATES AND 2-CHLORO-2'',6''DIETHYL N-METHOXYMETHYL)ACETANILIDE AND FURTHER CONTAINING A COMPOUND SELECTED FROM THE GROUP CONSISTING OF ARYL NALKYLCARBAMATE, ARYL N,N-DIALKYLCARBAMATE, ARYL NCYCLOALKYLCARBAMATE, AND MIXTURES THEREOF IN AN AMOUNT SUFFICIENT TO EXTEND THE SOIL LIFE OF SAID ALKYL N-PHENYLCARBAMATE OR MIXTURES OF ALKYL N-PHENYLCARBAMATES.
 2. A herbicidal composition containing herbicidally-effective amounts of both a. an alkyl N-phenylcarbamate or mixtures of alkyl N-phenylcarbamates represented by the structural formula
 3. The herbicidal composition of claim 2 wherein a. R1 contains from 1 to 8 carbon atoms; b. R2 is hydrogen, unsubstituted alkyl containing from 1 to 8 carbon atoms or haloalkyl containing from 1 to 8 carbon atoms; and c. R3 is unsubstituted alkyl containing from 1 to 8 carbon atoms, haloalkyl containing from 1 to 8 carbon atoms or cycloalkyl containing from 3 to 8 carbon atoms.
 4. The herbicidal composition of claim 3 which contains from about 0.1 to about 100 percent by weight actives.
 5. The herbicidal composition of claim 4 wherein a. the weight ratio of said alkyl N-phenylcarbamate or mixtures of said alkyl N-phenylcarbamates to said 2-chloro-2'',6''-diethyl N-(methoxymethyl)acetanilide present in the composition is in the range of from 1:500 to 500:1; and b. the weight ratio of said alkyl N-phenylcarbamate of mixtures of said alkyl N-phenylcarbamates to said compound or mixtures of said compounds present in the composition is in the range of from 1:1 to 100:1.
 6. The herbicidal composition of claim 5 wherein said alkyl N-phenylcarbamate is isopropyl N-phenylcarbamate.
 7. The herbicidal composition of claim 6 wherein said compound is selected from the group consisting of halophenyl N-alkylcarbamate, halophenyl N,N-diallylcarbamate, and halophenyl N-cycloalkylcarbamate.
 8. The herbicidal composition of claim 6 wherein said compound is selected from the group consisting of 4-chlorophenyl N-alkylcarbamate, 4-chlorophenyl N,N-dialkylcarbamate, and 4-chlorophenyl N-cycloalkylcarbamate.
 9. The herbicidal composition of claim 6 wherein said compound is selected from the group consisting of phenyl N-methylcarbamate, 4-chlorophenyl N-methylcarbamate, 4-chlorophenyl N-ethylcarbamate, 4-chlorophenyl N,N-dimethylcarbamate, 4-chlorophenyl N-butylcarbamate, 4-chlorophenyl N-cyclohexylcarbamate and 1-naphthyl N-methylcarbamate.
 10. The herbicidal composition of claim 5 wherein said alkyl N-phenylcarbamate is isopropyl N-(3-chlorophenyl)carbamate.
 11. The herbicidal composition of claim 10 wherein said compound is selected from the group consisting of halophenyl N-alkylcarbamate, halophenyl N,N-dialkylcarbamate, and halophenyl N-cycloalkylcarbamate.
 12. The herbicidal composition of claim 10 wherein said compound is selected from the group consisting of 4-chlorophenyl N-alkylcarbamate, 4-chlorophenyl N,N-dialkylcarbamate, and 4-chlorophenyl N-cycloalkylcarbamate.
 13. The herbicidal composition of claim 10 wherein said compound is selected from the group consisting of phenyl N-methylcarbamate, 4-chlorophenyl N-methylcarbamate, 4-chlorophenyl N-ethylcarbamate, 4-chlorophenyl N,N-dimethylcarbamate, 4-chlorophenyl N-butylcarbamate, 4-chlorophenyl N-cyclohexylcarbamate, and 1-naphthyl N-methylcarbamate.
 14. A method of controlling weeds comprising applying to soil containing weeds a. a herbicidal amount of an alkyl N-phenylcarbamate or mixtures of alkyl N-phenylcarbamates; b. a herbicidal amount of 2-chloro-2'',6''-diethyl N-(methoxymethyl)acetanilide; and c. a compound or mixture of compounds selected from the group consisting of aryl N-alkylcarbamate, aryl N,N-dialkylcarbamate, and aryl N-cyclohexylcarbamate in an amount sufficient to extend the soil life or said alkyl N-phenylcarbamate or mixtures of alkyl N-phenylcarbamates.
 15. The method of claim 14 wherein said alkyl N-phenylcarbamate or mixtures of alkyl N-phenyl carbamates is applied at a rate in the range of from 0.1 to 50 pounds per acre, said 2-chloro-2'',6''-diethyl N-(methoxymethyl)acetanilide is applied at a rate in the range of from 0.1 to 50 pounds per acre and the compound or mixture of compounds is applied at a rate which is from 1 to 100 percent of the rate at which the alkyl N-phenylcarbamate is applied.
 16. The method of claim 15 wherein the application is a pre-emergence application.
 17. The method of claim 15 wherein said alkyl N-phenylcarbamate or mixtures of alkyl N-phenylcarbamates are selected from the group consisting of isopropyl N-phenylcarbamate and isopropyl N-(3-chlorophenyl)carbamate and said compound or mixtures of compounds are selected from the group consisting of phenyl N-methylcarbamate, 4-chlorophenyl N-methylcarbamate, 4-chlorophenyl N-ethylcarbamate, 4-chlorophenyl N-butylcarbamate, 4-chlorophenyl N,N-dimethylcarbamate, 4-chlorophenyl N-cyclohexylcarbamate, and 1-naphthyl N-methylcarbamate.
 18. A herbicidal composition containing herbicidally-effective amounts of both isopropyl N-phenylcarbamate and 2-chloro-2'',6''-diethyl N-(methoxymethyl)acetanilide and further containing 4-chlorophenyl N-methylcarbamate in an amount sufficient to extend the soil life of said isopropyl N-phenylcarbamate.
 19. A herbicidal composition containing herbicidally-effective amounts of both isopropyl N-(3-chlorophenyl)carbamate and 2-chloro-2'',6''-diethyl N-(methoxymethyl)acetanilide and further containing 4-chlorophenyl N-methylcarbamate in an amount sufficient to extend the soil life of said isopropyl N-(3-chlorophenyl) carbamate.
 20. A herbicidal liquid concentrate comprising about 33.5 percent by weight isopropyl N-(3-chlorophenyl) carbamate, about 33.5 percent by weight 2-chloro-2'',6''-diethyl N-(methoxymethyl)acetanilide, about 8.3 percent by weight 4-chlorophenyl N-methylcarbamate and about 14.1 percent by weight xylene. 